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Journal articles on the topic 'Damascenone'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Naiker, Mani. "β-Damascenone-yielding precursor(s) from Cabernet Sauvignon grapes." South Pacific Journal of Natural and Applied Sciences 19, no. 1 (2001): 11. http://dx.doi.org/10.1071/sp01003.

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β-Damascenone, a potent aroma component of in a variety of grapes and wines, has a sensory threshold of approximately 2ng/L in water. This C13 norisoprenoid ketone is principally generated from hydrolyzable precursors, which was glycosidically bound. Isolation of β-damascenone-yielding precursors from Cabernet Sauvignon grape skins using C18 reversed phase chromatography followed by droplet countercurrent chromatography yielded multiple chromatographically distinguishable precursor fractions. The existence of multiple precursors was further evident from the varying ratios of 3-hydroxy- β-damascone (the by-product): β-damascenone generated upon acid hydrolysis of the chromatographically distinguishable precursor fractions.

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2

Tomasino, Elizabeth, and Shiloh Bolman. "The Potential Effect of β-Ionone and β-Damascenone on Sensory Perception of Pinot Noir Wine Aroma." Molecules 26, no. 5 (February 27, 2021): 1288. http://dx.doi.org/10.3390/molecules26051288.

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Volatile compounds are responsible for driving the aroma of wine. Because of their low perception thresholds, norisoprenoids may play an important role in wine aroma. Studies have shown that β-damascenone may act as an aroma enhancing compound. However, the direct impact on wine aroma is unclear. Our study examined the direct impact of β-ionone and β-damascenone on the aroma sensory perception of Pinot noir wines. Triangle tests were used to determine if assessors could distinguish between wines with varying concentrations of β-ionone and β-damascenone in three different Pinot noir wine matrixes. Descriptive analysis was performed on these treatments, perceived as different in triangle tests. Results show that β-ionone acts as a significant contributor to aromas in Pinot noir wine, as individuals could differentiate both the low and high concentration wines from the control. How β-ionone impacted wine aroma depends on the wine matrix, as different aroma descriptors were affected based on the model wine used, resulting in floral, red berry or dark berry aromas. The effect of β-damascenone on Pinot noir aroma was less clear, as perception seems to be heavily influenced by wine matrix composition. This study contributes to our understanding of the complex chemical causation of fruity aromas in Pinot noir wine.

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3

Lapczynski, A., J. Lalko, D. McGinty, S. Bhatia, C. S. Letizia, and A. M. Api. "Fragrance material review on damascenone." Food and Chemical Toxicology 45, no. 1 (January 2007): S172—S178. http://dx.doi.org/10.1016/j.fct.2007.09.056.

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4

Ni, Hui, Qing-Xiang Jiang, Ting Zhang, Gao-Ling Huang, Li-Jun Li, and Feng Chen. "Characterization of the Aroma of an Instant White Tea Dried by Freeze Drying." Molecules 25, no. 16 (August 10, 2020): 3628. http://dx.doi.org/10.3390/molecules25163628.

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The aroma of an instant white tea (IWT) was extracted through simultaneous distillation–extraction (SDE) and analyzed by sensory evaluation, gas chromatography-mass spectrometry-olfactometry (GC-MS-O), aroma reconstruction, omission test and synergistic interaction analysis. Sensory evaluation showed the IWT was dominated with floral and sweet notes. The SDE extract had the aroma similar to the IWT. The main volatile components in the SDE extract were benzyl alcohol, linalool, hotrienol, geraniol, α-terpineol, coumarin, camphene, benzeneacetaldehyde, 2-hexanone, cis-jasmin lactone and phenylethyl alcohol. GC-MS-O and aroma reconstruction experiments showed 16 aroma-active compounds. Linalool, trans-β-damascenone and camphene were the major contributors to floral, sweet and green notes based on flavor dilution analysis and omission test. Linalool and trans-β-damascenone had synergistic effect to promote floral and sweet notes. Camphene and trans-β-damascenone had synergistic effect to reduce green and sweet notes. The study helps to understand the aroma of IWT and antagonism interactions among aroma-active volatiles.

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5

Li, Zhihua, Ling Dong, Jin Jeon, So Young Kwon, Chi Zhao, and Hyung-Hee Baek. "Characterization and Evaluation of Aroma Quality in Doubanjiang, a Chinese Traditional Fermented Red Pepper Paste, Using Aroma Extract Dilution Analysis and a Sensory Profile." Molecules 24, no. 17 (August 27, 2019): 3107. http://dx.doi.org/10.3390/molecules24173107.

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Doubanjiang, a Chinese traditional fermented red pepper paste, is eaten worldwide for its unique flavor. The objective of this study was to evaluate the aroma quality of doubanjiang using solvent-assisted flavor evaporation (SAFE) and headspace solid-phase microextraction (HS-SPME) coupled with gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA). A total of 165 volatile compounds, belonging to 13 chemical classes, were identified. Esters and hydrocarbons were the predominant groups. Thirteen aroma-active compounds were detected by AEDA of SAFE and HS-SPME, and their odor activity values (OAVs) were calculated by dividing their concentration by their odor threshold in water. Among them, ethyl isovalerate, β-damascenone, 3-isobutyl-2-methoxypyrazine (IBMP), and sotolone had the highest OAVs (>1000). In addition, sotolone, methional, β-damascenone, 3-isobutyl-2-methoxypyrazine, ethyl isovalerate, phenylethyl alcohol and linalool had high flavor dilution (FD) factors. Sotolone, β-damascenone and 3-isobutyl-2-methoxypyrazine were identified for the first time in doubanjiang and played significant roles in its aroma quality.

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6

Rögner, Nadine S., Veronika Mall, and Martin Steinhaus. "Odour-active compounds in liquid malt extracts for the baking industry." European Food Research and Technology 247, no. 5 (March 11, 2021): 1263–75. http://dx.doi.org/10.1007/s00217-021-03707-z.

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AbstractAn odorant screening by gas chromatography–olfactometry (GC–O) and a crude aroma extract dilution analysis (AEDA) applied to the volatiles isolated from a light and a dark liquid malt extract (LME) by solvent extraction and solvent-assisted flavour evaporation (SAFE) identified 28 odorants. Fifteen major odorants were subsequently quantitated and odour activity values (OAVs) were calculated as ratio of the concentration to the respective odour threshold value (OTV). Important odorants in the light LME included 3-(methylsulfanyl)propanal (OAV 1500), (E)-β-damascenone (OAV 430), and 4-ethenyl-2-methoxyphenol (OAV 91). In the dark LME, sotolon (OAV 780), 3-(methylsulfanyl)propanal (OAV 550), (E)-β-damascenone (OAV 410), acetic acid (OAV 160), and maltol (OAV 120) were of particular importance. To get an insight into the changes during malt extract production, the quantitations were extended to the malt used as the starting material for both LMEs. Addition of a minor amount of water to malt before volatile extraction was shown to be effective to cover the free as well as the bound malt odorants. Results showed that some LME odorants originated from the starting material whereas others were formed during processing. Important process-induced LME odorants included (E)-β-damascenone and 4-ethenyl-2-methoxyphenol in the light LME as well as maltol, sotolon, (E)-β-damascenone, and 2-methoxyphenol in the dark LME. In summary, the odorant formation during LME production was shown to be more important than the transfer of odorants from the malt.

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7

Yamano, Yumiko, Yasuko Watanabe, Naoharu Watanabe, and Masayoshi Ito. "Stereocontrolled synthesis of glucosidic damascenone precursors." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (November 15, 2002): 2833–44. http://dx.doi.org/10.1039/b208758h.

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8

Skouroumounis, George K., Ralph A. Massy-Westropp, Mark A. Sefton, and Patrick J. Williams. "Precursors of damascenone in fruit juices." Tetrahedron Letters 33, no. 24 (June 1992): 3533–36. http://dx.doi.org/10.1016/s0040-4039(00)92682-0.

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9

Popova, Venelina, Tanya Ivanova, Tsvetko Prokopov, Milena Nikolova, Albena Stoyanova, and Valtcho D. Zheljazkov. "Carotenoid-Related Volatile Compounds of Tobacco (Nicotiana tabacum L.) Essential Oils." Molecules 24, no. 19 (September 23, 2019): 3446. http://dx.doi.org/10.3390/molecules24193446.

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Tobacco (Nicotiana tabacum L.) aroma is an important attribute of tobacco quality and is influenced by a variety of minor chemical components, including carotenoid degradation products. The objectives of this work were to determine the content of the most important fragrance-shaping carotenoid degradation products in the essential oils (EOs) of the three types of Bulgarian tobacco—Oriental (OR), flue-cured Virginia (FCV), and Burley (BU)—and to compare them with other aromatic products from tobacco. The content of total carotenoids and β-carotene was highest in BU tobacco (22.23 and 20.34 mg/100 g DW, respectively), followed by OR (13.60 and 12.09 mg/100 g DW in variety “Plovdiv 7” (Pd7); 6.27 and 5.45 mg/100 g DW in “Krumovgrad” (Kr), and FCV (5.93 and 3.73 mg/100 g DW). EOs were obtained by hydrodistillation in an acidified medium, and the main aroma-impact compounds from carotenoid degradation (identified by GC-MS) were as follows: FCV-α-ionone (0.61 mg/100 g DW), dihydro-β-ionone (0.96 mg/100 g DW), β-damascenone (1.26 mg/100 g DW); BU-α-ionone (0.73 mg/100 g DW), dihydro-β-ionone (1.19 mg/100 g DW), β-damascenone (1.35 mg/100 g DW); OR(Kr)-α-ionone (0.20 mg/100 g DW), β-ionone (1.08 mg/100 g DW), dihydro-β-ionone (1.34 mg/100 g DW), β-damascenone (0.36 mg/100 g DW); OR(Pd7)-α-ionone (1.43 mg/100 g DW), dihydro-β-ionone (1.73 mg/100 g DW), β-damascenone (1.23 mg/100 g DW). Ionone and its derivatives were not identified in the aroma extraction products concrete, resinoid, or absolute. The results suggest that temperature, pH of the medium, process duration, and possibly other unknown factors affect carotenoid transformation. The study provides insight into the composition of tobacco EOs and may be of interest to the fragrance industry.

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10

Sefton, MA, GK Skouroumounis, RA Massywestropp, and PJ Williams. "Norisoprenoids in Vitis vinifera White Wine Grapes and the Identification of a Precursor of Damascenone in These Fruits." Australian Journal of Chemistry 42, no. 12 (1989): 2071. http://dx.doi.org/10.1071/ch9892071.

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Twenty-four norisoprenoids , which are either free volatile components of juices of Vitis vinifera cvv . Chardonnay, Semillon and Sauvignon Blanc, or are liberated by glycosidase enzyme, or acid hydrolysis of extracts of these juices, have been identified. Eleven of these norisoprenoids are reported as grape products for the first time. The hypothetical 7-oxomegastigmane precursors, grasshopper ketone (5) and megastigm-5-en-7-yne-3,9-diol (10), as well as the related allene, 9-hydroxymegastigma-4,6,7-trien-3-one (6), have been observed for the first time, cooccurring with damascenone (1), 3-hydroxy- β- damascone (2) 3-oxo-β-damascone (3) and 3-oxo-α-damascone (4). Hydrolytic studies have shown that megastigm-5-en-7-yne-3.9-diol (10) is a precursor of damascenone (1) and 3-hydroxy- β- damascone (2) during wine conservation.

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11

Chaumont-Olive, Pauline, Jorge Sánchez-Quesada, Ana María Collado Pérez, and Janine Cossy. "Synthetic approaches to the damascone and damascenone isomers." Tetrahedron 82 (February 2021): 131932. http://dx.doi.org/10.1016/j.tet.2021.131932.

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12

Daniel, Merran A., Carolyn J. Puglisi, Dimitra L. Capone, Gordon M. Elsey, and Mark A. Sefton. "Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and Their Analogues, in both Aglycone and Glycoconjugate Forms." Journal of Agricultural and Food Chemistry 56, no. 19 (October 8, 2008): 9183–89. http://dx.doi.org/10.1021/jf8018134.

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13

Daniel, Merran A., Carolyn J. Puglisi, Dimitra L. Capone, Gordon M. Elsey, and Mark A. Sefton. "Rationalizing the Formation of Damascenone: Synthesis and Hydrolysis of Damascenone Precursors and their Analogues, in both Aglycone and Glycoconjugate Forms." Journal of Agricultural and Food Chemistry 57, no. 4 (February 25, 2009): 1654. http://dx.doi.org/10.1021/jf900248h.

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14

Daniel, Merran A., Gordon M. Elsey, Dimitra L. Capone, Michael V. Perkins, and Mark A. Sefton. "Fate of Damascenone in Wine: The Role of SO2." Journal of Agricultural and Food Chemistry 52, no. 26 (December 2004): 8127–31. http://dx.doi.org/10.1021/jf048582h.

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15

Pineau, Bénédicte, Jean-Christophe Barbe, Cornelis Van Leeuwen, and Denis Dubourdieu. "Which Impact for β-Damascenone on Red Wines Aroma?" Journal of Agricultural and Food Chemistry 55, no. 10 (May 2007): 4103–8. http://dx.doi.org/10.1021/jf070120r.

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16

Puglisi, Carolyn J., Gordon M. Elsey, Rolf H. Prager, George K. Skouroumounis, and Mark A. Sefton. "Identification of a precursor to naturally occurring β-damascenone." Tetrahedron Letters 42, no. 39 (September 2001): 6937–39. http://dx.doi.org/10.1016/s0040-4039(01)01411-3.

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17

Yoshizaki, Yumiko, Kazunori Takamine, Shogo Shimada, Kayo Uchihori, Kayu Okutsu, Hisanori Tamaki, Kiyoshi Ito, and Yoshihiro Sameshima. "The Formation of β-Damascenone in Sweet Potato Shochu." Journal of the Institute of Brewing 117, no. 2 (2011): 217–23. http://dx.doi.org/10.1002/j.2050-0416.2011.tb00464.x.

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18

Slaghenaufi, Davide, Anita Boscaini, Alessandro Prandi, Andrea Dal Cin, Vittorio Zandonà, Giovanni Luzzini, and Maurizio Ugliano. "Influence of Different Modalities of Grape Withering on Volatile Compounds of Young and Aged Corvina Wines." Molecules 25, no. 9 (May 3, 2020): 2141. http://dx.doi.org/10.3390/molecules25092141.

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Withering is a practice traditionally used in various regions to produce sweet or dry wines. During withering there is an increase in sugar content but also a modification in volatile compound profiles. Controlling metabolic changes through the dehydration process to obtain wines with desired characteristics is therefore a challenging opportunity. The effects of two different withering technologies, post-harvest or on-vine with blocked sap vessel flow, on the volatile profile of young and aged Corvina red wines was investigated. The results showed that modulation of wine aroma due to the withering process is associated with fermentative metabolites, such as esters, higher alcohols, and acids, as well as grape-related compounds such as C6 alcohols, terpenes and norisoprenoids. Significant differences were also found by comparing the two withering techniques. Post-harvest in a traditional “fruttaio” warehouse wines showed higher content of ethyl acetate, ethyl butanoate, β-citronellol and 3-oxo-α-ionol, whereas post-harvest withering on-vine increased β-damascenone in wines. The type of withering technique has an influence on the evolution of some aroma compounds during the aging of wine, among them linalool, (E)-1-(2,3,6-trimethylphenyl)buta-1,3-diene (TPB), n-hexyl acetate, ethyl acetate, ethyl 3-methylbutanoate, 3-oxo-α-ionol and β-damascenone.

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19

Straubinger, Markus, Holger Knapp, Noriaki Oka, Naoharu Watanabe, and Peter Winterhalter. "Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals." Journal of Agricultural and Food Chemistry 45, no. 10 (October 1997): 4053–56. http://dx.doi.org/10.1021/jf970278j.

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20

Lloyd, Natoiya D. R., Dimitra L. Capone, Maurizio Ugliano, Dennis K. Taylor, George K. Skouroumounis, Mark A. Sefton, and Gordon M. Elsey. "Formation of Damascenone under both Commercial and Model Fermentation Conditions." Journal of Agricultural and Food Chemistry 59, no. 4 (February 23, 2011): 1338–43. http://dx.doi.org/10.1021/jf103741n.

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21

Joshi, Rajesh K. "Chemical Composition of the Essential Oil of Croton bonplandianus from India." Natural Product Communications 9, no. 2 (February 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900234.

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The essential oil obtained from the aerial parts of Croton bonplandianus Baill. was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of 37 compounds have been identified, representing 96.2% of the total oil. The main constituents were identified as β-caryophyllene (16.7%), germacrene D (14.7%), borneol (8.3%), Z-β-damascenone (6.(%), isobornyl acetate (6.2%), α-humulene (6.1%), germacrene A (5.2%) and caryophyllene oxide (4.5%). The oil was rich in sesquiterpene hydrocarbons (60.1%).

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22

Awale, Mani, Connie Liu, and Misha T. Kwasniewski. "Workflow to Investigate Subtle Differences in Wine Volatile Metabolome Induced by Different Root Systems and Irrigation Regimes." Molecules 26, no. 19 (October 3, 2021): 6010. http://dx.doi.org/10.3390/molecules26196010.

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To allow for a broad survey of subtle metabolic shifts in wine caused by rootstock and irrigation, an integrated metabolomics-based workflow followed by quantitation was developed. This workflow was particularly useful when applied to a poorly studied red grape variety cv. Chambourcin. Allowing volatile metabolites that otherwise may have been missed with a targeted analysis to be included, this approach allowed deeper modeling of treatment differences which then could be used to identify important compounds. Wines produced on a per vine basis, over two years, were analyzed using SPME-GC-MS/MS. From the 382 and 221 features that differed significantly among rootstocks in 2017 and 2018, respectively, we tentatively identified 94 compounds by library search and retention index, with 22 confirmed and quantified using authentic standards. Own-rooted Chambourcin differed from other root systems for multiple volatile compounds with fewer differences among grafted vines. For example, the average concentration of β-Damascenone present in own-rooted vines (9.49 µg/L) was significantly lower in other rootstocks (8.59 µg/L), whereas mean Linalool was significantly higher in 1103P rootstock compared to own-rooted. β-Damascenone was higher in regulated deficit irrigation (RDI) than other treatments. The approach outlined not only was shown to be useful for scientific investigation, but also in creating a protocol for analysis that would ensure differences of interest to the industry are not missed.

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23

Baderschneider, Beate, George Skouroumounis, and Peter Winterhalter. "Isolation of Two Glucosidic Precursors of β-Damascenone from Riesling Wine." Natural Product Letters 10, no. 2 (May 1997): 111–14. http://dx.doi.org/10.1080/10575639708043724.

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24

Näf, Regula, Alain Velluz, and Walter Thommen. "Isolation of a glucosidic precursor of damascenone from lycium halimifolium mil." Tetrahedron Letters 31, no. 45 (January 1990): 6521–22. http://dx.doi.org/10.1016/s0040-4039(00)97106-5.

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25

Pongprayoon, U., P. Baeckström, U. Jacobsson, M. Lindström, and L. Bohlin. "Antispasmodic Activity of β-Damascenone andE-Phytol Isolated fromIpomoea pes-caprae." Planta Medica 58, no. 01 (February 1992): 19–21. http://dx.doi.org/10.1055/s-2006-961381.

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26

Puglisi, Carolyn J., Gordon M. Elsey, Rolf H. Prager, George K. Skouromounis, and Mark A. Sefton. "ChemInform Abstract: Identification of a Precursor to Naturally Occurring β-Damascenone." ChemInform 33, no. 1 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200201228.

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27

Vujanovic, Milena, Sasa Djurovic, and Marija Radojkovic. "Chemical composition of essential oils of elderberry (Sambucus nigra L.) flowers and fruits." Acta Periodica Technologica, no. 52 (2021): 229–37. http://dx.doi.org/10.2298/apt2152229v.

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The majority of essential oils obtained from medicinal plants have been demonstrated to be effective in the treatment of different kinds of diseases, and they are increasingly used in the diet. Due to their chemical composition, essential oils are a very interesting product of the secondary metabolism of plants, for both consumers and researchers. Among others, elderberry (Sambucus nigra L.) is mostly a woody plant, while it can rarely be found as a herbaceous perennial plant. This plant species has been used in traditional medicine because it is a very rich source of phytochemicals. The aim of this study was to identify and compare the composition of essential oils obtained from flowers and fruits of this plant, collected from the Balkan Peninsula. The oils were obtained using the Clevenger apparatus, and their composition was evaluated by gas chromatography - mass spectrometry (GC-MS). The oil composition was affected by the part of the plants used: the most abundant bioactive compounds in the essential oil of air-dried elderberry fruits were ?-damascenone (35.70%) and linalyl anthranilate (24.15%). ?-damascenone was the dominant compound in the essential oil of lyophilized elderberry fruits (38.64%), while linalool was detected in the concentration of 32.80%. In the essential oil of air-dried elderflowers, the most abundant compound was carane (13.19%). The essential oils of S. nigra shown substantial chemical composition and could be used as a potential source of natural products in the cosmetics and food industry.

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28

Methner, Yvonne, Philipp Dancker, Robin Maier, Mailen Latorre, Mathias Hutzler, Martin Zarnkow, Martin Steinhaus, Diego Libkind, Stephanie Frank, and Fritz Jacob. "Influence of Varying Fermentation Parameters of the Yeast Strain Cyberlindnera saturnus on the Concentrations of Selected Flavor Components in Non-Alcoholic Beer Focusing on (E)-β-Damascenone." Foods 11, no. 7 (April 2, 2022): 1038. http://dx.doi.org/10.3390/foods11071038.

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The diversification of beer flavor is becoming increasingly popular, especially in the field of non-alcoholic beers, where sales are growing steadily. While flavor substances of traditional beers can largely be traced back to defined secondary metabolites, the production of non-alcoholic beers with non-Saccharomyces yeasts generates novel fruity flavors, some of which cannot yet be assigned to specific flavor substances. In a recently published study, besides pear, cool mint sweets, and banana-like flavor, distinctive red berry and apple flavors were perceived in a non-alcoholic beer fermented with the yeast strain Cyberlindnera saturnus TUM 247, whose secondary metabolites were to be elucidated in this study. The trials were carried out using response surface methodology to examine the fermentation properties of the yeast strain and to optimize the beer with maximum fruitiness but minimal off-flavors and ethanol content. It turned out that a low pitching rate, a moderate fermentation temperature, and an original gravity of 10.5 °P gave the optimal parameters. Qualitative analysis of the secondary metabolites, in addition to standard analysis for traditional beers, was first performed using headspace-gas chromatography with olfactometry. (E)-β-damascenone emerged as the decisive substance for the red berry and apple flavor and so this substance was then quantitated. Although (E)-β-damascenone is a well-known secondary metabolite in beer and this substance is associated with apple or cooked apple- and berry-like flavors, it has not yet been reported as a main flavor component in non-alcoholic beers.

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29

Bruno, Maurizio, Azzurra Milia, Giorgia Catinella, and Svetlana Bancheva. "Volatile Components from Aerial Parts of Centaurea diffusa and C. micrantha ssp. melanosticta and Their Biocidal Activity on Microorganisms Affecting Historical Art Crafts." Natural Product Communications 13, no. 9 (September 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300920.

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The chemical composition of the essential oils from aerial parts of two taxa of Centaurea belonging to subgenus Acrolophus, Centaurea diffusa Lam. and C. micrantha Hoff. ssp. melanosticta (Lange) Dostàl, respectively collected in Croatia and Spain, were evaluated by GC and GC-MS. The main components of C. diffusa were hexadecanoic acid (31.1%), ( Z,Z)-9,12-octadecadienoic acid (10.7%) and damascenone isomers (6.4%), whereas hexahydrofarnesyl acetone (27.8%), hexadecanoic acid (8.3%) and caryophyllene oxide (6.4%) were the most abundant components of C. micrantha ssp. melanosticta. The oils showed good antibacterial and antifungal activities against some microorganisms that infest historical art works.

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30

Chevance, Fabienne, Christine Guyot-Declerck, Jérôme Dupont, and Sonia Collin. "Investigation of the β-Damascenone Level in Fresh and Aged Commercial Beers." Journal of Agricultural and Food Chemistry 50, no. 13 (June 2002): 3818–21. http://dx.doi.org/10.1021/jf020085i.

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31

Puglisi, Carolyn J., Merran A. Daniel, Dimitra L. Capone, Gordon M. Elsey, Rolf H. Prager, and Mark A. Sefton. "Precursors to Damascenone: Synthesis and Hydrolysis of Isomeric 3,9-Dihydroxymegastigma-4,6,7-trienes." Journal of Agricultural and Food Chemistry 53, no. 12 (June 2005): 4895–900. http://dx.doi.org/10.1021/jf050327p.

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32

Kinoshita, Tomomi, Satoshi Hirata, Ziyin Yang, Susanne Baldermann, Emiko Kitayama, Shigetaka Matsumoto, Masayuki Suzuki, Peter Fleischmann, Peter Winterhalter, and Naoharu Watanabe. "Formation of damascenone derived from glycosidically bound precursors in green tea infusions." Food Chemistry 123, no. 3 (December 2010): 601–6. http://dx.doi.org/10.1016/j.foodchem.2010.04.077.

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33

Yuan, Qunchen, Chunlian Qin, Saisai Zhang, Jianguo Wu, Yong Qiu, Changming Chen, Liquan Huang, Ping Wang, Deming Jiang, and Liujing Zhuang. "An In Vitro HL-1 Cardiomyocyte-Based Olfactory Biosensor for Olfr558-Inhibited Efficiency Detection." Chemosensors 10, no. 6 (May 24, 2022): 200. http://dx.doi.org/10.3390/chemosensors10060200.

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Some short-chain fatty acids with a pungent or unpleasant odor are important components of human body odor. These malodors severely threaten human health. The antagonists of malodors would help to improve odor perception by affecting the interaction between odors and their receptors. However, the traditional odor detection and analysis methods, such as MOS, electrochemical, conductive polymer gas sensors, or chromatography-mass spectrometry are not suitable for screening the antagonists since they are unable to detect the ligand efficacy after odor-receptor binding. In this study, RT-PCR results showed that HL-1 cardiomyocytes endogenously express the olfactory receptor 558 (Olfr558) which can be activated by several malodorous short-chain fatty acids. Therefore, an in vitro HL-1 cardiomyocyte-based olfactory biosensor (HCBO-biosensor) was developed by combining cardiomyocytes and microelectrode array (MEA) chips for screening the potential antagonists of the Olfr558. Firstly, it showed that the biosensor specifically responded to ligands of Olfr558 through odor stimulation experiments. Then, an odor response model of HL-1 cardiomyocytes was constructed by a ligand of Olfr558 (isovaleric acid). The response feature of the in vitro HCBO-biosensor to individual odors and mixtures with a potential antagonist (citral or β-damascenone) were extracted and compared. Finally, the Olfr558-inhibited efficiency was indirectly detected by comparing the half-maximal inhibitory concentration of isovaleric acid. The results showed that β-damascenone greatly inhibited Olfr558 while citral showed no significant inhibitory effect. In conclusion, we built a novel screening method for the antagonists of Olfr558 based on HL-1 cardiomyocytes and the MEA chip which will assist odor-related companies to develop novel antagonists of Olfr558.

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34

Sen, Alina, Gudrun Laskawy, Peter Schieberle, and Werner Grosch. "Quantitative determination of .beta.-damascenone in foods using a stable isotope dilution assay." Journal of Agricultural and Food Chemistry 39, no. 4 (April 1991): 757–59. http://dx.doi.org/10.1021/jf00004a028.

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35

Boulin, Bertrand, Martine Taran, Bernadette Arreguy‐San Miguel, and Bernard Delmond. "New Preparation Methods for α‐Damascone, γ‐Damascone, and β‐Damascenone using Pyronenes." Synthetic Communications 37, no. 15 (August 2007): 2579–91. http://dx.doi.org/10.1080/00397910701462898.

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36

Weyerstahl, Peter, and Kai Licha. "Structure-Odor Correlation, XXIV. Synthesis and Olfactory Properties of Damascone and Damascenone Analogs." Liebigs Annalen 1996, no. 5 (January 25, 2006): 809–14. http://dx.doi.org/10.1002/jlac.199619960527.

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37

Rodriguez, Silvana A., and Ana P. Murray. "Antioxidant Activity and Chemical Composition of Essential Oil from Atriplex Undulata." Natural Product Communications 5, no. 11 (November 2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501132.

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The essential oil from aerial parts (stems and leaves) of Atriplex undulata (Moq) D. Dietr. (Chenopodiaceae) has been studied for its in vitro antioxidant activity. The chemical composition of the oil obtained by hydrodistillation was determined by GC and GC-MS. The major constituents were p-acetanisole (28.1%), β-damascenone (9.3%), β-ionone (5.1%), viridiflorene (4.7%) and 3-oxo-α-ionol (2.2%). The antioxidant activity of the oil was determined by two methods: Crocin bleaching inhibition (Krel= 0.72 ± 0.15) and scavenging of the DPPH radical (IC50 = 36.2 ± 1.6 μg/mL). The presence of active compounds like p-acetanisole, carvone, vanillin, 4-vinylguaiacol, guaiacol, terpinen-4-ol and α- terpineol could explain the antioxidant activity observed for this oil.

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38

Kutney, James P., Philip J. Gunning, Robin G. Clewley, John Somerville, and Steven J. Rettig. "The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues." Canadian Journal of Chemistry 70, no. 7 (July 1, 1992): 2094–114. http://dx.doi.org/10.1139/v92-266.

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Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues. The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2). In addition, thujone-derived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues. In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed. In summary, these studies afford an attractive versatile route to these important perfumery materials.

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39

Jerković, Igor, Marina Kranjac, Marina Zekić, Ani Radonić, and Zvonimir Marijanović. "The Application of Headspace Solid-phase Microextraction as a Preparation Approach for Gas Chromatography with Mass Spectrometry." Kemija u industriji 69, no. 9-10 (2020): 515–20. http://dx.doi.org/10.15255/kui.2020.020.

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Reviewed in brief are the selected results of the application of headspace solid-phase microextraction as a preparative approach for gas chromatography – mass spectrometry (HS-SPME/GC-MS) for natural organic compounds research at the University of Split, Faculty of Chemistry and Technology. A wide variety of headspace compounds from different natural sources has been identified: lower aliphatic compounds (e.g., C5- and C6-compounds), aromatic compounds, monoterpenes (e.g., linalool derivatives (oxides, anhydro-oxides, epoxides), hotrienol), sesquiterpenes (e.g., eudesmol isomers, hydrocarbons), and C9- and C13-norisoprenoids (e.g., 3,4-dihydro-3-oxoedulan, 4-oxoisophorone, trans-β-damascenone). These compounds are important phytochemicals as flavour/fragrance compounds, chemical markers of the botanical origin or others (e.g., allelochemicals, pheromones, or acaricide residue).

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40

Mosaferi, Shabnam, Rebecca E. Jelley, Bruno Fedrizzi, and David Barker. "Synthesis of d6-deuterated analogues of aroma molecules-β-damascenone, β-damascone and safranal." Results in Chemistry 4 (January 2022): 100264. http://dx.doi.org/10.1016/j.rechem.2021.100264.

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41

Gijs, Laurence, Fabienne Chevance, Vesna Jerkovic, and Sonia Collin. "How Low pH Can Intensify β-Damascenone and Dimethyl Trisulfide Production through Beer Aging." Journal of Agricultural and Food Chemistry 50, no. 20 (September 2002): 5612–16. http://dx.doi.org/10.1021/jf020563p.

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42

KOBAYASHI, Hironori, and Yasuaki KATSUNO. "Effect of Processing on β-Damascenone Content in Wine and Application to Winemaking." Journal of Japan Association on Odor Environment 41, no. 3 (2010): 181–87. http://dx.doi.org/10.2171/jao.41.181.

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43

Yuan, Fang, R. Paul Schreiner, and Michael C. Qian. "Soil Nitrogen, Phosphorus, and Potassium Alter β-Damascenone and Other Volatiles in Pinot noir Berries." American Journal of Enology and Viticulture 69, no. 2 (January 8, 2018): 157–66. http://dx.doi.org/10.5344/ajev.2017.17071.

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44

Carneiro, J. R., J. A. Ferreira, L. F. Guido, P. J. Almeida, J. A. Rodrigues, and A. A. Barros. "Determination of β-damascenone in alcoholic beverages by reversed-phase liquid chromatography with ultraviolet detection." Food Chemistry 99, no. 1 (January 2006): 51–56. http://dx.doi.org/10.1016/j.foodchem.2005.07.024.

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45

Azenha, Manuel, Borys Szefczyk, Dianne Loureiro, Porkodi Kathirvel, M. Natália D. S. Cordeiro, and António Fernando-Silva. "Computational and Experimental Study of the Effect of PEG in the Preparation of Damascenone-Imprinted Xerogels." Langmuir 29, no. 6 (January 29, 2013): 2024–32. http://dx.doi.org/10.1021/la304706t.

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46

Roberts, Deborah D., Alex P. Mordehai, and Terry E. Acree. "Detection and Partial Characterization of Eight .beta.-Damascenone Precursors in Apples (Malus domestica Borkh. Cv. Empire)." Journal of Agricultural and Food Chemistry 42, no. 2 (February 1994): 345–49. http://dx.doi.org/10.1021/jf00038a021.

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47

Uddin, Ahmed N., Ivica Labuda, and Fredric J. Burns. "A novel mechanism of filaggrin induction and sunburn prevention by β-damascenone in Skh-1 mice." Toxicology and Applied Pharmacology 265, no. 3 (December 2012): 335–41. http://dx.doi.org/10.1016/j.taap.2012.08.035.

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48

Sefton, Mark A., George K. Skouroumounis, Gordon M. Elsey, and Dennis K. Taylor. "Occurrence, Sensory Impact, Formation, and Fate of Damascenone in Grapes, Wines, and Other Foods and Beverages." Journal of Agricultural and Food Chemistry 59, no. 18 (September 28, 2011): 9717–46. http://dx.doi.org/10.1021/jf201450q.

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49

WEYERSTAHL, P., and K. LICHA. "ChemInform Abstract: Structure-Odor Correlation. Part 24. Synthesis and Olfactory Properties of Damascone and Damascenone Analogues." ChemInform 27, no. 38 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199638191.

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50

Carbone, Katya, Giulia Bianchi, Maurizio Petrozziello, Federica Bonello, Valentina Macchioni, Barbara Parisse, Flora De Natale, Roberta Alilla, and Maria Carla Cravero. "Tasting the Italian Terroir through Craft Beer: Quality and Sensory Assessment of Cascade Hops Grown in Central Italy and Derived Monovarietal Beers." Foods 10, no. 9 (September 3, 2021): 2085. http://dx.doi.org/10.3390/foods10092085.

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The present study aimed to chemically and sensorially characterize hop samples, cv Cascade, grown in two different Italian regions (Latium and Tuscany) as well as their derived beers by a multi analytical approach. Significant differences in bitter acid, oil and polyphenol content were observed for hop samples according to their origin. Gas chromatography-olfactometry analysis pointed out floral notes for Tuscany samples, where hops from Latium were characterized by spicy and resinous notes, correlated to the presence of sesquiterpenes. Differences in the molecular fingerprinting were also highlighted by Fourier–Transform Infrared Spectroscopy. The differences found in the hops were reflected in the beers, which were clearly recognized as distinct by a sensory panel. Both beer samples were mainly characterized by six aroma compounds (linalool, geraniol and β-damascenone, citronellol, 2-phenylethyl acetate, and 2-phenylethanol), three of which were potentially responsible for the geographic origin of the hops given their significantly different concentrations.

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